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I would have some Bards in the leadership. Bards are only a blink away from being rogues anyway.
But if you're going to go for the Big Surprise, have a Cleric or a Druid as a crime boss.
A warlock due to high charisma and maybe a fey patron or a homebrew patron
A group of street toughs running a "protection" racket on locals to not get beat up by street toughs.
I would have some Bards in the leadership. Bards are only a blink away from being rogues anyway.
But if you're going to go for the Big Surprise, have a Cleric or a Druid as a crime boss.
A warlock due to high charisma and maybe a fey patron or a homebrew patron
A group of street toughs running a "protection" racket on locals to not get beat up by street toughs.